Shortly after the February 2014 Euromaidan revolution which ousted pro-Russian Ukrainian President Viktor Yanukovych, Russia orchestrated a rapid and mostly bloodless annexation of the Crimea. Following the removal of Ukrainian authority from the peninsula, the Kremlin focused simultaneously on legitimizing the annexation via an electoral reform in Crimea and fermenting political unrest in the Donbas. As violence broke out in the Donbas, anti-Ukrainian government militias were formed by defecting Ukrainian security forces members, local volunteers, and volunteers from Russia. The Kremlin provided extensive support for these militias which sometimes even came in the form of direct military intervention by conventional Russian forces. However, the use of state-sponsored militias by Russia is not a new phenomenon. Since the end of the Cold War, the Russian Federation has been relying on militias to help stabilize local security environments, and more recently, achieve foreign security policy objectives in the Near Abroad. By tracking the history of Vostok (East) Battalion during its two distinctly different iterations, first as a militia for the Yamadayev family which operated primarily in Chechnya as well as briefly in South Ossetia and Lebanon and then as separatist formation in Eastern Ukraine, my thesis seeks to examine why Russia uses militias. Using the theoretical frameworks of principle-agent relations and organizational hierarchy, my thesis examines post-Soviet military reforms to contextualize the Kremlin's rationale for utilizing militia groups as well as analyzing the costs and benefits Moscow ultimately incurs when it leverages militias as force projection assets domestically and in the Near Abroad. / Master of Arts / This thesis is an examination of Russia’s relationship with its proxy militias. Proxy militias are paramilitary formations comprised of a mix of civilians and military veterans which states use to carry out acts of coercive violence without having to rely on regular military forces. Specifically, the thesis is divided into two case studies of a unit known as Vostok Battalion. Vostok has existed in two distinctly different iterations; first as a Chechen based militia operating throughout the Caucuses and later as a rebel militia fighting the Ukrainian government in the Donbas region. In both cases, Vostok received support and varying levels of guidance from Russia. The case studies of this thesis are attempting to contextualize why Russia utilizes proxy militias and identify the challenges Russia faces when its ability to control them is degraded.